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Preheat oven to 450F degrees.
Add tomatoes, onions, garlic, olive oil, 1 tsp salt and Italian seasoning to a large dutch oven and toss.
Turn all the tomatoes cut side up and then place in the oven for 1 hour.
Remove from the oven and use a blender or immersion blender to blend the tomatoes up.
Stir in heavy cream, remaining salt, sugar, butter, and a few cranks fresh cracked pepper.
Taste and add more salt and pepper if needed.
Finish with a sprinkle of fresh basil before serving.
Add two slices of Colby jack to 4 slices of bread and then evenly distribute the shredded unexpected cheddar on top.
Add the remaining bread to the top then smear ½ tbsp of butter on the top of each sandwich.
Heat a large fry pan over medium and place the sandwiches in, butter side down.
Smear the rest of the butter over the top of the sandwiches while they’re cooking.
Once the bottoms are golden brown, carefully flip the sandwiches and cook the other side; about 4 minutes on each side.
Once golden brown on all sides and the cheese has melted, remove from heat and serve with tomato soup.